Reaktion #497713

Reaktionsgleichung

dicyclopropylmethanone

n-Butyllithium

thiazole

→

dicyclopropyl(1,3-thiazol-2-yl)methanol

Ausbeute 93.0%

Lösungsmittel

THF

THF

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.STIRRINGthe mixture was stirred 30 min at −78° C.
2. 2
   Sonstigeto reach room temperature
3. 3
   SonstigeThe reaction was quenched by addition of water
4. 4
   Extraktionthe mixture was extracted with ethyl acetate (3×)
5. 5
   WaschenThe combined organic fractions were washed with brine
6. 6
   Trocknendried (Na2SO4)
7. 7
   Filtrationfiltered
8. 8
   Sonstigethe solvent was evaporated under reduced pressure
9. 9
   SonstigeThe residue was purified by chromatography on silica gel (0-100% ethyl acetate in hexanes)

Vorschrift

n-Butyllithium (2.5 M in hexanes, 0.953 mL, 2.38 mmol) was added to a stirred, cooled −78° C. mixture of thiazole (0.169 mL, 2.383 mmol) in THF (5.0 mL) and the mixture was stirred at −78° C. for 15 min. A solution of the dicyclopropylmethanone (250 mg, 2.27 mmol) in THF (3.0 mL) was added dropwise and the mixture was stirred 30 min at −78° C. and then the temperature was allowed to reach room temperature. The reaction was quenched by addition of water and the mixture was extracted with ethyl acetate (3×). The combined organic fractions were washed with brine, dried (Na2SO4), filtered and the solvent was evaporated under reduced pressure. The residue was purified by chromatography on silica gel (0-100% ethyl acetate in hexanes) to give dicyclopropyl(1,3-thiazol-2-yl)methanol (412 mg, 2.110 mmol, 93% yield). MS APCI: [M-OH]+ m/z 179.0.

Quelle